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Nickel‐Catalyzed Cross‐Coupling of Redox‐Active Esters with Boronic Acids
Author(s) -
Wang Jie,
Qin Tian,
Chen TieGen,
Wimmer Laurin,
Edwards Jacob T.,
Cornella Josep,
Vokits Benjamin,
Shaw Scott A.,
Baran Phil S.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605463
Subject(s) - chemistry , alkyl , catalysis , redox , functional group , nickel , combinatorial chemistry , coupling reaction , organic chemistry , boronic acid , suzuki reaction , palladium , polymer
A transformation analogous in simplicity and functional group tolerance to the venerable Suzuki cross‐coupling between alkyl‐carboxylic acids and boronic acids is described. This Ni‐catalyzed reaction relies upon the activation of alkyl carboxylic acids as their redox‐active ester derivatives, specifically N ‐hydroxy‐tetrachlorophthalimide (TCNHPI), and proceeds in a practical and scalable fashion. The inexpensive nature of the reaction components (NiCl 2 ⋅6 H 2 O—$9.5 mol −1 , Et 3 N) coupled to the virtually unlimited commercial catalog of available starting materials bodes well for its rapid adoption.